Triethylamine → HCID 67126145, compound

HRID 514045Notes

Reaction equation

HRID 514045 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:30])[C:6]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:7]2[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.[CH3:31][N:32]([CH3:36])[CH2:33][C:34]#[CH:35].C(N(CC)CC)C>O1CCCC1.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:26]([O:25][CH:19]([C:6]1[C:5]([CH3:30])=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[C:35]#[C:34][CH2:33][N:32]([CH3:36])[CH3:31])[C:7]=1[C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH3:27])([CH3:28])[CH3:29]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 81643N,N-Dimethylpropargylamine3×HCID 67126073HCID 67126073, compound

Product 1

HCID 67126145HCID 67126145, compoundYield 6.6%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalyst2×HCID 178418476HCID 178418476, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 2-(5-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate (100 mg, 0.20 mmol) and N,N-dimethylprop-2-yn-1-amine (0.065 mL, 0.61 mmol) in anhydrous tetrahydrofuran was added copper iodide (8 mg, 0.04 mmol) and PdCl2(PPh3)2 (14 mg, 0.02 mmol). The reaction was heated to 100° C. overnight. After cooling to room temperature the reaction was charged with PdCl2(PPh3)2 (14 mg, 0.02 mmol), copper iodide (8 mg, 0.04 mmol), N,N-dimethylprop-2-yn-1-amine (0.065 mL, 0.61 mmol) and triethylamine (1 mL). The reaction was heated to 100° C. overnight. To the reaction was then added N,N-dimethylprop-2-yn-1-amine (0.065 mL, 0.61 mmol) and heated to 100° C. overnight. The crude reaction mixture was absorbed onto silica gel and purified by flash column chromatography (silica gel, ethyl acetate/hexanes, methanol/ethyl acetate) to give a yellow oil (6.5 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C30H35ClNO3: 492.22; found: 492.15.

Workup

  1. temperatureAfter cooling to room temperature the reaction
  2. temperatureThe reaction was heated to 100° C. overnight
  3. customThe crude reaction mixture
  4. customwas absorbed onto silica gel
  5. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes, methanol/ethyl acetate)

Sources & evidence

ORD record
ord-6bdba0c0e9f9440995459ee3d4f52c72
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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